


To New Beginnings

by St_Jimmy_Is_Dead



Category: Supernatural
Genre: Bisexual Dean, Castiel is a Novak, F/M, Gay Castiel, Implied Relationships, Implied/Referenced Alcohol Abuse/Alcoholism, John Winchester's A+ Parenting, M/M, Older Castiel, Professor AU, Professors, References to Castiel/Other(s), References to Dean/Other(s), Relationship(s), Younger Dean
Language: English
Status: In-Progress
Published: 2016-03-05
Updated: 2016-10-20
Packaged: 2018-05-24 22:57:53
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 18,363
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6170020
Author URL: https://archiveofourown.org/users/St_Jimmy_Is_Dead/pseuds/St_Jimmy_Is_Dead
Summary: <blockquote class="userstuff">
              <p>Dean might have moved around a lot as he grew up, but he only ever stayed in one place long enough for it to grow on him. That is, until he gets a job as a professor in a university in Chicago, Illinois. Moving away from his brother and his family and friends seemed risky, but sooner than he expected, he learned to love the city. But as he grows older, he starts realizing that he is running out of time; and just when he thinks he has hit rock bottom, everything falls into place. What will he do when he finds himself in a situation he never expected to be in?</p><p>-- ON HIATUS DUE TO STUDIES. THERE WILL STILL BE A FEW UPDATES HERE AND THERE, BUT THEY WON'T BE REGULAR UPDATES. --</p>
            </blockquote>





	1. No One Knows

**Author's Note:**

> Um... so this is my first fanfic on Ao3, and I really don't know if it's any good. Anyways, I hope you guys like this, and leave comments if you have suggestions/constructive criticism; it'll help me grow as a writer :)  
> The first chapter looks back at Dean's first day in Chicago, and is most likely going to be the only time I write a chapter that isn't in the current year.  
> Enjoy!

_ **9th of August 2012** _

It was around seven in the morning when Dean finally pulled out of the parking lot of his small home in Lawrence, Kansas. He was still having a hard time believing everything that was happening to him; one moment he was sitting on his couch at home, and the next he was at the Roadhouse, celebrating his new job with his family and friends. None of them believed he would be accepted, but he didn’t blame them, because he never thought he would get the job, either. Professor of English Language and Literature in the University of Chicago. The blond smiled at himself as he leaned back into the car seat, the music filling the empty space in his car.

The sun was shining brightly as he sang along to a tune by Night Ranger, his grin growing and growing the further he drove. Chicago, Illinois. What the hell was he going to do in Chicago? Sure, his family moved around a lot when he was young, but they had never been in one place for too long. Lawrence was the only place he truly knew, but now he was going to have to try to impress his colleagues and his students. Usually he’d be fine with it; after all, he only had to charm his way into their hearts, and that wasn’t too hard for him. Then again, this wasn’t just another day at the bar, he wasn’t picking up chicks, or guys, or both, and then leaving them. Dean was going to be a role model for his students, and he needed to make sure he was on his best behavior.

The song faded and soon ‘Bad Reputation’ by Joan Jett was blasting through the speakers of his car, and all he could do was laugh at how attached he felt to his song (not that he would ever let Sam know that, because his brother would never let that go). But his hyperactivity fizzed out shortly after he thought about his brother, and his lips twitched into a small, sad smile. The only time they were ever living in separate places was when he was in Stanford, but Dean had the rest of his family then. Now Sammy had their family and Jess, and there would probably be a baby on the way sooner rather than later. He thought back to his last conversation with his brother, chewing on his lower lip as he stared blankly at the road ahead of him. _‘Hey, how great would it be if you got to watch “Chicago” live while living in Chicago?’_ Sam had chirped as he helped him load all of his stuff into the trunk of his car. _‘Shuddup, Samantha, I don’t have time for your weird obsession with musicals, alright?’_ Dean had huffed, but he was looking at his brother with a bright spark in his eyes.

It was a place for him to start over again. He could be whoever he wanted to be, and he didn’t have to worry about people judging him for his reputation or his childhood. He was just Dean Winchester, or Professor Winchester, and nothing more. Eight more hours and he would be the new and improved Dean Winchester, and in exactly twenty-four hours, he’d introduce himself to his students as Professor Winchester for the first time. He turned up the volume and smiled sadly to himself as he got closer to leaving Lawrence.

“To new beginnings,” he mumbled, patting the steering wheel as he began driving faster.

* * *

One of the other reasons why Dean was so excited to move to Chicago was their deep-dish pizza. He loved food, anyone who knew him personally knew that far too well, and a Chicago deep-dish pizza was basically a pizza pie. And boy did he love his pies. Also, they didn't stare at him weirdly when he asked if he could have one to take back to his apartment. In fact, they were more than happy to bring him one, and they even did so quickly. It was easy for him to say that his first hour in Chicago was already fantastic.

According to Sammy, there were thirty-seven movable bridges in the city alone, and he soon realized that the guy wasn’t exaggerating with the number. Not that he minded, really, because it gave him time to stare at the water, which was mindbogglingly blue. He was fairly certain that it was the bluest blue that he’d ever seen in his entire life, and it was mesmerizing. It shone beautifully in the daylight, and Dean almost completely forgot about the fact that the only reason he had time to stare at it was because he was waiting for the bridge to come back down. The only reason he remembered he had to move was because of some asshole right behind him who kept on honking his horn, but Dean didn’t mind. This city was turning out to be far better than he had ever expected.

He arrived at his new apartment building a few minutes later, where he knew his stuff was already waiting for him, because the moving company had brought all of his possessions in a few days earlier. The blond nervously opened the door once he parked his car in the lot, and he grabbed his bag. This was it. He was about to see his new home, and he was freaking out over nothing. Okay, maybe it wasn’t nothing, but it certainly wasn’t a big deal. He was just going to see his apartment for the first time; it wasn’t like he was meeting his students today. He got into the elevator and made his way up to the sixth floor before walking down the hallway and towards his new apartment. Fishing the key out of his pocket, he let his bag drop to the floor, and he quickly attempted to unlock the door. He frowned when he couldn’t get it to open, and tried over and over again until a calm voice behind him spoke up. “You mind if I help you with that?”

Dean turned around to look at the source of the sound, and his lips twitched up into a smile. The man had short brown hair and icy blue eyes, but his smile was sweet and friendly. He was burly and slightly shorter than Dean, though he wouldn’t have noticed it had he not been checking out the stranger. Oh, God, he was checking out the stranger. He attempted to hide the way his face flushed and he nodded, clearing his throat. “Yeah, I’d like that. I’m kinda scared that the landlord gave me the wrong key.”

The stranger smiled and nodded, holding his hand out. “Give me the key, I’ll get the door open in no time. These locks are just old and rusty, it’ll take you time to get used to ‘em.” The man spoke quickly, and Dean knew that if he didn’t move around as often as he had, he would barely be able to understand what he was saying in his thick Louisiana accent. The lock clicked and Dean’s eyes lit up, feeling his body relax slightly. “There you go, told you I’d be able to do it.”

“Thanks, man. I thought I’d be locked out on my first day in the city,” he laughed, picking up his bag and taking the key back from him.

“Don’t worry, I wouldn’t let that happen to my new neighbor. “ His hand was stretched out towards him all of a sudden, and the warm smile on his lips spread further. “The name’s Benny Lafitte.”

“Dean Winchester. It’s nice to meet you, neighbor,” he hummed, taking the other’s hand and smiling at him in return.

“You’re new here, huh?”

“Yessir. Just got a job at the University of Chicago.”

Benny let out an impressed whistle and cocked his head, looking him up and down. “That’s real fancy. So, professor, how about I take you out for a drink tonight? Show you the best bar in town?” Dean’s face must have shown his surprise at the man’s straightforwardness, because the brunette was soon shaking his head and laughing. “Oh, no, brother, didn’t mean it like that. I’ve got a girl, don’t worry about me hitting on you. I just meant that you’re new here; I’m guessing it’d be nice for you to find some friends early on?”

Dean let out a sigh that caused his whole body to slouch. “Oh, uh, yeah. That sounds great, Benny. Just knock on my door at any time this evening, and we’ll go out,” he confirmed, hesitating before patting him on the back.

“Great! I’ll see you soon, then,” the man commented, and quickly disappeared into the apartment across the hall.

The Winchester grabbed his bag and made his way into his own apartment, taking in the space with parted lips. It wasn’t anything impressive, really, but it was to Dean. After living in motel rooms nearly his entire life, moving to a new city and living in an actual apartment was a dream come true. He had his own kitchen, a toilet, a bathroom, one bedroom, and a giant living room. He didn’t have to share it with Sammy, or his dad, or Jo, or Ash, or anybody. This was his own home. And he absolutely loved it.

He was getting ready to start unpacking his things after he placed the deep dish pizza in the fridge that the apartment came with, but he found himself sitting down on his couch instead. He would have to move it a bit later, but for now, he was okay with sitting exactly where it was placed. Or maybe even laying down… He ended up taking a nap, his arm tucked under his head and the buttons of his flannel undone as the sun began to set outside his living room windows.

* * *

Benny had woken him up from his nap at around eight-thirty. He had only gotten to his new house at around four in the afternoon, meaning he had slept for five hours. He told him to give him a moment before he quickly changed into a t-shirt and another pair of jeans, and joined him in the hallway sooner than he thought he would. They talked about their home states, what brought them to Illinois, and what they did as they walked towards the bar. Once they reached the bar, they were already deep into conversation about their families and friends.

Dean learned that Benny’s girlfriend lived with him, and that her name was Andrea. The only reason Dean hadn’t met her yet was because she was visiting her family in Greece for the past week, and she would only return on Monday, which was the following day. Benny had learned that Dean was bisexual and that although he was thirty-three years old, he only had one relationship that really meant something to him in his life with a woman named Lisa.

Benny was a mechanic, and Dean nearly freaked out when he heard that because that had been his job all throughout college. The two spoke frantically about their love for cars for what they thought was only a few minutes, but soon it was time for them to go back to their apartments. So they walked back to the building slowly, both of them enjoying how easy it was to talk to one another until they returned to the sixth floor of the apartment building.

“Thanks for tonight, man. I was really stressed about being here, you know?”

“Don’t worry about it, brother. You’re gonna have one hell of a hangover tomorrow morning, so just go sleep it off on your couch. I’ll help you set up your bed and the rest of the apartment tomorrow, alright?”

“Yeah, alright. See you tomorrow, Benny.”

“Good night, Winchester.” And with that, the brunette was gone. His door clicked shut, forcing Dean to walk back towards his own.

He stripped out of his jeans and his flannel before grabbing a blanket that he kept in his duffel (just in case he got into this sort of situation) and sat on the couch. He pulled off his shoes and his socks before lying down with a lazy smile tugging at his lips, the wall in front of him slowly blurring. Chicago was surprising him so far, and he was hoping that it wouldn’t stop. He drifted off soon enough, ignoring the sounds outside of his window as sleep took control of his weary body.


	2. Blue Eyes

**_ 24th of August 2015 _ **

It was only the first day of the new school year, and Dean was already exhausted. Though that might have something to do with the fact that he was starting his fourth year as a professor in the University of Chicago, and he wasn’t getting any younger.

 A lot of things had changed since he first moved to Chicago. He actually unpacked all of his boxes and settled into his house comfortably. He dated a guy named Aaron Bass for nearly two years before the man chose a job in Europe over him. Benny was his best friend, and he was the best man in his wedding. He met a girl named Charlie Bradbury who introduced him to things he never saw himself doing, like LARPing and hacking; he wasn’t too sure why he needed to know the latter, but he did anyways. He had a two and a half year old niece named Mary who he loved to bits waiting for him at his brother’s house in California, but at the same time was a constant reminder of how well his brother was doing. Sam was married, a father to one girl, and now had a boy on the way. He was a successful lawyer, was adored by his friends and family, and yet was still convinced that Dean was the perfect role model.

Benny had managed to convince him to go out to a bar the previous night, and Dean couldn’t help the lazy smile on his lips as he thought about it. It was like he was a college student again; getting drunk on school nights, complaining about his hangover to his friends the following morning, but keeping a lopsided grin stretched across his face as he greeted the people around him. The ones who weren’t supposed to know how much his head was pounding right now, but would still look at him as if he just kicked a puppy.

He managed to drag himself out of his bed and walk towards his chair, where his clothes for the day were already laid out. He had a green tie with white and black stripes, a white button down shirt and a pair of dark jeans. Who said jeans couldn’t look professional? Once he brushed his teeth and styled his hair, he pulled on the clothes and made his way towards the living room to find his car keys. He tried making himself some breakfast in his own kitchen once, but he ended up getting to work late, and it wasn’t exactly something he wanted to repeat. So instead he would go to the café near the campus and get himself a slice of pie and a cup of coffee. He knew that pie wasn’t exactly the best breakfast food, but after awhile of having it for breakfast, he realized he didn’t really care all that much. As long as he wasn’t hungry and grumpy, he would eat whatever the hell he wanted. 

Dean bought his meal for the morning and made his way through the halls, greeting a few of his students, stopping to chat with a few of the other professors as he passed, and nearly having a heart attack when Charlie screamed his name across the crowded hallway. The students were used to the way she acted and were very much aware of their friendship, so they weren’t exactly surprised when her voice broke through all of their conversations. They just paused momentarily before carrying on as if nothing happened.

“Dean Winchester! I cannot believe you and Benny didn’t call me last night!” She huffed as she stormed over, making Dean smile at her sheepishly.

“We wanted one last night to ourselves, Charlie. If it helps, we didn’t invite Andrea along, either.”

Charlie’s brows furrowed in her confusion, and she pouted before speaking, “Of course you didn’t invite Andrea along. Why would you want his wife there? Wouldn’t she just tell him to stop drinking after two beers?”

“Yeah, she probably would,” he laughed, rubbing his nape. “It’s nothing personal, Charlie, but I promise you that the next time we go out, you’ll be the first to hear about it.”

“I better be!” She chirped, and her eyes lit up. Dean couldn’t help but shake his head as he laughed, and he nudged her slightly before he motioned towards the end of the hall with his head.

“I’m going to head to my lecture room. I’ll see you later.” She pinched his cheek before finally letting him leave, and suddenly she was skipping down the hall like she was a kindergartner visiting her older sibling on campus. Though, to be fair, they were usually a whole lot cuter. Charlie sometimes came off as a bit more terrifying rather than cute, but he had gotten used to her, so he supposed he couldn’t really complain.

He stared after her for a while before snapping out of his trance and making his way towards the room, humming to himself as he opened the door with his elbow. Except when he stepped in, he wasn’t alone like he expected. Instead, he was greeted with a back turned towards him and the sound of chalk against a blackboard. He really hoped he would get used to that sound by now, but instead it made him wince as the man kept dragging the chalk against the dark surface. The guy might as well be holding Styrofoam, because it would send just as many shivers down his spine.

He looked around the lecture hall, wondering if he might have gotten the room wrong, but he knew that he didn’t. This was the place where he had been teaching English language and literature in for the past four years of his life. There was still a small crack in the wall by the projection screen, and there was one blue chair amongst all of the other maroon chairs in the room; he had placed it right in the middle, just so that it’d draw the most attention, and it always did. His students seemed to love fighting over it, and he enjoyed watching because he was still here for the entertainment, at the end of the day. It’s not as if his salary was really enough, so he might as well enjoy what he does even more than usual, right?

Dean squinted his eyes as he looked over the man, trying to see if anything about him reminded him of someone else who was on staff. Even if his clothes reminded him of some of the older professors, he couldn’t remember anyone with tousled dark brown hair. He waited for a few moments before clearing his throat, drawing the stranger’s attention. That was his first mistake. The man spun on his heel and locked eyes with him, and he felt himself go weak at his knees. He had the most brilliant blue eyes he’d ever seen, and if he thought the water in Chicago was a mesmerizing shade of blue, then it was nothing in comparison to this guy’s eye color. They shone even in the dim light of the lecture hall, and they were looking him up and down curiously, making him fidget slightly. His second mistake was attempting to speak to the guy. “I-- You-- My lecture hall-- Oh, Jesus Christ.” He couldn’t remember the last time someone attractive made him so nervous, but whoever this guy was was doing a hell of a good job at embarrassing him without saying a word. He swore he could see his lips twitch upwards just a tiny bit, though, at the way he was stuttering and God was it no doing his heart any good. 

“I believe you’re trying to tell me something, but I’m afraid I can’t quite understand you.” And his last mistake was being in the room and being able to hear him speak, because holy crap that voice was a voice he’d want to hear every night before he went to sleep. It was low, and gravely and it made Dean feel as though he was being wrapped up in a warm blanket. Which, of course, was a ridiculous thing to say. But then again, this man was making him do plenty of ridiculous things, and he didn’t even know who the hell this guy was.

“I, uh, yeah. I am trying to tell you something,” he said with an embarrassed laugh, wanting to rub his nape more than anything but not being able to due to his hands being occupied with his coffee and a box with apple pie in it. “It’s just that I think you’re in the wrong lecture hall. I’ve been teaching in this place for the past four years, and every year I’ve been teaching in this lecture hall,” he explained, chewing on his lower lip. He let himself take in the man’s sharp jaw and chapped lips, and his eyes drifted up slowly to his hair as he wondered what running his fingers through the dark locks would feel like. His first day of the year and he was already fantasizing about the newbie. Great.

He took in the man’s outfit, looking over the dark blue tie that caused his eyes to stand out, the smooth white fabric of the other’s shirt clinging onto him tightly and showing the lean muscle beneath it, dress pants that gave away the shape of is hips and his ass perfectly and made his whole body feel like it was melting. Sooner rather than later, he realized that the other began speaking, and he blushed a bright pink as he began paying attention.

“Oh,” the man mumbled, his brows scrunching in a way that made him look adorably confused before collecting all of his things. “I was directed to this room, I suppose I did just get it wrong. I hope I haven’t disrupted you in any way,” he said quickly, and before Dean was able to stop him to ask him what his name was, he was gone. The blond pouted as the door swung shut, but he didn’t stay sad for long. Instead, he walked straight to his desk and opened his box of pie, digging in almost immediately and letting out a pleased hum.

* * *

His students missed him, of course. They mostly talked about their summers, and what they were excited about for this year, and everyone had asked him to share about his personal life, because who doesn’t like hearing about what the old man did over the summer? He told them about how he spent time with Mary and drove to the beach with his family, and how he’d gotten to surf for the first time in years. A few of the girls giggled at that, and he had to try his hardest not to roll his eyes.

He knew many of them found him attractive, and it wasn’t that he didn’t find it flattering, but the problem was that it was inappropriate. He remembered Sam’s voice when he told him that over the break, and how surprised he was. It had stung a little, but he supposed he had a point; he wasn’t exactly known for caring about what relationships were and were not appropriate, so why would he suddenly care now? _“Because I’m a responsible adult, now, Sammy,”_ Dean had replied with an offended huff, crossing his arms over his chest protectively as his brother rolled his eyes.

He’d been hoping that hot-new-professor-guy would walk back into his classroom at some point during the day, claiming to have left something behind accidentally, but he never returned. Dean had walked up and down the halls, going into Charlie’s lecture hall and then Gabe’s and anyone else’s just in case he got to bump into the guy in the hallway at some point, but he never saw him. It made him feel oddly sad, and there was a small pang in his chest whenever he returned to his classroom unsuccessful.

It wasn’t until he made his way out to the parking lot that he finally caught a glimpse of the perfect brown locks that he had seen up close earlier that day, the ones that seemed to either be windswept, or disheveled due to sleep. He didn’t care why they looked the way they did, what he cared about was how someone’s hair managed to make them look so attractive like that man. The man whose name he still did not know, and craved to get closer to.

“Good God, Benny is going to make so much fun of me tonight,” he huffed once he slid into the Impala’s driver seat, balling his hands into fists and placing them in front of his eyes as he groaned in annoyance. Benny meant well, he knew that much, but boy was he a pain in the ass. But instead of stalling, he drove back towards his apartment, smile tugging widely at his lips as he thought of a certain blue-eyed man that managed to flip his world around within only a few seconds.


	3. A Man's Best Friend

**Summary for the Chapter:**

> This was actually a whole lot of fun to write, so I'm hoping it sounds as good as I think it does.  
> Here's a photo that shows what I think Doof looks like: https://s-media-cache-ak0.pinimg.com/236x/75/2c/89/752c897fd36ad5af93ebba976211a682.jpg  
> Cas will be back in the next chapter, don't worry.

**_ 9th of September 2015 _ **

He was just going to pick up snacks for Charlie’s hamster at the nearest PetSmart. He was going to step in, buy the treats at the counter, and step out. He never had a pet growing up, and he sure as hell didn’t need one now. 

Or, well, that was what he thought. One of the ladies asked him if he was interested in adopting a dog from one of the adoption agencies nearby, and he politely declined; but this lady seemed adamant, and when Dean began telling her that he couldn’t possibly get a dog, she began showing him pictures. There were pictures of every breed of dog, their ages ranging from newborn pups to ones who were probably past the age of ten. And as much as Dean wanted to refuse, he really couldn’t, because he wasn’t a monster; plus, his apartment was empty, and company from a pup didn’t sound all that bad. So he took down the address and thanked her, and barely hesitated as he pulled out of the parking space.

Dean stepped into the building awkwardly, looking around. He hadn’t quite thought about the fact that there would be cats in the area, and suddenly he was sneezing every other moment. Maybe this was a mistake.

Except it definitely wasn’t, because the moment he laid his eyes on one of the cages in the corner of the room, he felt his heart melt. He made his way past all of the cages with cats, ignoring how he was sneezing and instead letting his lips be tugged into a wide smile. The cage had a few puppies settled in it, and one of them was sound asleep on his side. He took a closer look at it, grinning widely as he noticed that only one of his ears had popped up. The other one was still down, and it was currently covering part of his shut eye. His little legs twitched, surprising Dean, but he relaxed as soon as the dog did, too, letting out a small sigh. The puppies around him were jumping up and down, but they weren’t drawing the man’s attention.

“He’s a corgi,” a voice behind him chirped, making Dean turn around to face whoever it was. The guy was sucking on a lollipop with an amused expression on his face, like he had seen the way Dean had been sneezing all the way until the cage. He was less than a head shorter than him, but he still felt like he was one of the shortest people he’d ever met. His nose was a bit crooked, his hair was about as long as Sammy’s was before he left Lawrence for Stanford, and his lips seemed to be stuck in a permanent smirk behind the sucker.

The blond looked over him once more before clearing his throat to speak up. “Does he have a name?”

“He does indeed. We call him Doof; short for ‘doofus’. He’s one hell of a clumsy dog. Keeps on tripping over his little paws when we take them out to the park to run. He’s pretty damn obedient, though. Doesn’t quite know what we’re saying, but he’s smart enough to be able to tell when we’re happy with him and when we aren’t.” He pulled the lollipop out of his mouth, eliciting a wet _pop_ that made the blond wrinkle his nose. “You can always rename him if you adopt him. He’s only four months old.”

“Four months? Shouldn’t the other ear have popped up yet?" 

“It takes time. If the ear doesn’t pop up by the time he’s nine months old, it may never pop up. Is that a problem?”

His eyes widened and he began sputtering, shaking his head. “What? No! I’m, uh, just confused, I guess. Never seen a full grown corgi with floppy ears.”

Gabriel shrugged nonchalantly, placing the lollipop back on his tongue. “Well, you’ve got nothing to worry about. As long as he’s taken care of, he’ll be just as fine as the other dogs.”

Dean’s eyes narrowed on the man’s nametag before he spoke up again, a small smile playing at his lips. “Well, Gabriel, I think Doof’s about to find a new home,” he said after a while, and the shorter man’s eyes lit up.

“Well, follow me, Mr…”

“Winchester. Dean Winchester.”

“Right, Dean Winchester. Let’s get you a dog.”

* * *

Gabriel helped him with everything he needed to get before he actually got to take Doof. It was a ridiculous name, but boy, he loved it. They got him a medium sized crate that would probably last forever, seeing as corgis usually weren’t that large when they finished growing in size, and Dean wasn’t exactly picky on whether the dog would get on the couch or not. He bought a few chew toys, treats, a bowl for water and another one for food, and a bag of food that Gabe had recommended, before finally getting him a red collar and a leash.

He told him about how he wasn’t entirely potty trained, but he was also learning not to go on anywhere that wasn’t a completely flat surface. When Dean asked what he meant by that, Gabriel told him that he’d only ever seen the dog wet the floor and not a couch or a piece of furniture. Dean let out a loud sigh of relief at that.

The shorter man made sure to tell Dean a number of times about the dog’s vaccinations, and he gave him addresses of a wide range of vets once they were at the counter paying for everything. He smirked at him as he swiped his credit card, clearing his throat.

“You look real nervous, Gabe. You’ve got nothing to worry about, he’s in good hands.”

“I know, I just wanna make sure you know what you’re doing, Winchester. Don’t want a cute puppy like him to fall into the wrong hands.”

Dean nodded in agreement, letting out a low hum. Gabe helped him bring everything into the Impala, except for the crate, which they left on the counter. Once they were back in the building, they made their way towards the dog’s cage, where Doof was already awake.

He was positively glowing at the sight of the dog marching around, his front left leg stepping in time with his back right leg, and his other legs doing the same. Gabriel reached into the cage gingerly, and Dean placed the crate on the ground before he reached out for the dog. His fur was soft, and he had to admit that he was fairly surprised that he wasn’t barking at him. Hell, he wasn’t even trying to bite him. He just looked up at him curiously, as if he was trying to figure out who he was, before he began squirming in his hold.

“Oh boy, okay, into the crate,” Dean said once he realized he was fighting a losing battle with the pup, and he quickly kneeled in front of the crate. He set the puppy down in front of it, letting out a soft breath, and he was surprised when he jumped right back towards him. His front paws were placed on his knee, and he let out a small bark that made his lips tug into a wide grin.

“I think he likes you,” Gabriel hummed from where he was standing.

“I sure as hell hope he does,” Dean replied, and he reached over to scratch behind his popped up ear. He helped the dog into the crate quickly after that, and he closed the small door behind him. Doof curled up almost immediately, and Dean let out a sigh of relief before standing up with the crate in his hand. “Thanks for your help today, Gabe. If I ever need anything, I’ll definitely come back here.”

“You better,” the shorter man huffed, sticking out a hand for a handshake. “Take good care of Doof, you hear me? You just adopted one of the sanest dogs around here.”

Dean shook his hand firmly, smiling brightly. “Don’t worry; I could use a sane pal,” he joked, looking down at the dog who was already fast asleep.

They went their separate ways after that. Dean returned home, and Gabe went back to work. The elder Winchester had called his friend and asked him for help with bringing everything upstairs, and Benny looked at him like he was completely mad once he got to the car.

“Really, brother? A dog?”

“Hey, I need some company, too, you know.”

“You never even mentioned you wanted one!”

“Well, I didn’t know I wanted one! Plus, I know how hard this is gonna be, but it’ll be worth it, man. I mean, how could I possibly say no to a puppy? So sue me, it’s just one impulse purchase.” He locked his car once Benny got the bag of food and the chew toys, and he took the rest of the things in his other hand. They made their way towards the elevator of their building in silence, and didn’t speak until they reached his front door.

“Dean, this isn’t even an impulse purchase! It’s an impulse _adoption_. Don’t you think that’s a bit strange?” Benny asked, looking at his friend worriedly.

“Benny, look at the dog for a second,” he said as he unlocked the door. They stepped into the apartment, and Dean dropped all of the things he’d been holding in his other hand onto the ground. He opened Doof’s crate and let the dog jump out, smiling at the dog’s yips. The corgi stopped by Benny’s foot, sniffing at it suspiciously before he went on to run around the living room.

Dean could tell that Benny was doing his best to hide a small smile that was tugging at his lips, and he stood back up, crossing his arms over his chest triumphantly.

“Fine, the pup’s pretty darn cute, you happy?”

“Extremely. Now keep an eye on Doof while I go store all of his stuff. Also, put his collar on him.” And with that, Dean disappeared into the kitchen. He had plenty of empty drawers and cabinets below his counter, meaning he had plenty of space for the dog’s snacks and food. He held up a bag of treats that he didn’t remember getting from Gabriel before he nearly smacked himself in the head. He sprinted towards the house phone, earning himself a confused look for Benny who was sitting on the couch with Doof on his lap.

 _“About time, Winchester! Where are my hamster’s treats?”_ Charlie asked, her voice sounding tired and annoyed.

“Here, with me. Uhm, listen, I’m sorry it took so long. Do you think I could give them to you tomorrow during work?”

There was a long pause on the other end of the line, but he could hear her sigh in defiance. _“Fine, but you better have a good excuse.”_

“Oh, I have a great excuse,” he assured her, biting back a laugh as he caught Benny’s startled expression. Doof was trying to jump up the man’s chest, and his friend seemed to be surprised by the amount of energy coming from the four-month-old pup.

_“Oh, yeah? Let’s hear it, then.”_

“I adopted a dog.” There was a long pause on the other side, and Dean was worried that Charlie was just as against the idea as Benny had been. “Charlie? You still there?”

The silence on the other side of the line was cut by a loud shriek of excitement that made Dean jump, and he let out a loud huff as he tried to calm himself. “Jesus Christ, warn me next time you do that, will you?”

_“Ohmygod, ohmygod, ohmygodddd! What kind of dog!?”_

“He’s a corgi.”

_“You’re totally going to let me dog-sit him once or twice or more, right?”_

Dean let out a loud laugh at that, and he feigned a thoughtful hum. “I don’t know… Don’t think I’m ready for him to be spoiled yet.”

“Dean!” Both of his friends called his name at the same time, and the blond let out yet another laugh 

“Look, Charlie, I’ll see you tomorrow. I think Benny needs me to save his ass.” Charlie let out a huff and hung up with that, and Dean quickly placed the phone back in its stand. He made his way over to Benny and picked up Doof from his lap, placing the dog in his own.

“He’s only cute for a certain amount of time,” Benny grumbled, but Dean recognized the fond look in the brunette’s eyes.

“Pretty sure you said the same thing about me to Andrea the first time you introduced us,” he chuckled, making the other man laugh softly as well. He felt the man pat his shoulder, and he looked up.

“Take him on a walk before you go to bed, alright? And remember to feed him; don’t want your dog to starve to death.” He watched the other man walk towards the door to his apartment, and he smiled at him, petting the dog’s head slowly.

“Welcome home, Doof,” Dean murmured once the door clicked shut.

* * *

 

Dean returned from his walk with Doof at around eight, and he left the door to the balcony open for him just enough so that he could go out if he needed to. The railing was made out of glass and was half his height, meaning it was three feet tall, so there was no way that his dog was falling out.

He filled one of his bowls with food and poured water into the other one before settling on the couch and turning on the television. He didn’t really notice when Doof settled down next to his thigh on the couch, but he chuckled when he noticed he had managed to fall asleep yet again. His legs were twitching as he dreamed, and Dean kept on looking between the puppy and his TV screen for the rest of the night.

He’d been sure that it had only been a few minutes, but the next time he looked up at the clock on his wall, it read ten-thirty. He pet the dog slowly, causing him to wake up, and he made his way around the apartment to make sure everything was in place. He could hear the dog’s small feet tap against the floor as he followed him closely, peering at him as he slid the door to the balcony close, and standing a few feet behind him when he locked the front door. He turned the lights off in the living room and in the kitchen before calling the dog, smiling as he watched him jump towards him, and he picked him up before he made his way to his bedroom. He set him down on his bed, and quickly disappeared into the bathroom to change into his pajamas. When he walked back out, however, Doof was spread out on one of the pillows, but luckily it wasn’t his own. He settled down on his side of the bed and plugged his phone into his charger before setting it down on the bedside table, turning off the lights and drifting off as he listened to the small puffs of air leaving the pup’s small body.


	4. You Really Got Me

**Notes for the Chapter:**

> So you guys seem to like this so far which is GREAT, so here's another chapter.  
> I hope this isn't bad, I wasn't really able to read over it and edit it because I've had a busy week.  
> I might make edits to things in the future, but it won't be to the story itself (except for the fact that Dean now teaches English language and literature instead of classical studies).  
> Anyways, enjoy!

**_ 2nd of October 2015 _ **

Weeks passed by before Dean laid his eyes on the hot-new-professor-guy again. He had given up on asking his coworkers about him, and he even ignored the fact that now half of his students were fully aware of the fact that he was bisexual and was harboring a massive crush on the stranger. They would smirk at him in class as though they were the only ones who knew his secret in the entire world, and not as if he addressed the entire room when bringing up the stranger. 

He had tried forgetting about him in every way possible. He’d gone to a bar with Benny plenty of times only to leave early with a girl or a guy draped over his arm, he’d contacted Aaron and Lisa (Aaron had been more than happy to open the photos Dean had drunkenly sent him. Lisa… not so much), he curled up on the couch next to Doof who was quickly growing, and he’d even let Charlie talk him into watching some chick flick with her while eating a tub of ice cream (although he didn’t entirely hate it, especially since he managed to talk her into getting him some pie, too). He was doing everything he could to get this guy out of his mind, and it was driving him absolutely crazy. He had only met him once, and the other guy hadn’t even said anything interesting.

“‘Oh, I was directed to this room, I suppose I did just get it wrong.’ Yeah, you think?” Dean mocked angrily as he unlocked the door to the apartment. Doof was jumping right next to his leg, his paws occasionally landing on his shoe, but he didn’t mind; he had to deal with Sammy stepping on him for a majority of his life, and he was way heavier than his dog.

Dean had even given him a name in his mind. His name was James, but he called him Jimmy. Jimmy was two years older than him, had no siblings and was an absolute genius. He moved to Chicago after teaching in some fancy university in Europe, knows how to speak Spanish, French and Italian (he also knows a few words in German), and knows how to cook so well that Dean’s cooking skills are horrifyingly bad compared to his. He knew that there was no way that any of the things he thought about the man were true, but what could he do? If he couldn’t see the guy and talk to him himself, he might as well make things up to satisfy his curiosity. Not that it helped, really, but he did try his best.

It was a chilly Friday afternoon in the beginning of October. He said goodbye to Doof, patted his head and made sure that the balcony door was closed. He opened up one window, though, just so that the dog would have some fresh air, and refilled his water and food bowls. Ignoring his dog was always the hardest part of leaving; Doof would whimper and follow him around closely, and he continuously promised him that he would be back, because why the hell would he leave his dog all alone? He locked the door behind him, ignoring the thumps of Doof’s paw against the door as he made his way to the elevator.

The trip to the repair shop was short, but he still managed to freeze in the short amount of time he spent outside of his car or a building. He had his jacket wrapped around himself tightly, and he even had a coat somewhere in the trunk in case he ended up deciding he couldn’t handle the weather. Dean Winchester wasn’t made for cold weather, and even after living on the planet for thirty-six years, he still wasn’t used to the cold breezes that swept through the country every fall. To make it even worse, Chicago was also known as ‘Windy City’, meaning Dean was constantly shivering when he was outside. If his hair looked even remotely good that day, it would appear terribly windswept once he stepped out of his car and walked towards his next destination, and he definitely didn’t enjoy having his hair messed with.

Usually on Fridays he would pop into the garage to help Benny with work. Not because he had lost a bet to him and now had to work on cars for free every Friday for as long as he lived in the city, but because he actually enjoyed working on cars by his best friend’s side. Besides, this had been the one place where he was able to completely ignore ‘Jimmy’ ever since he first saw him.

He stepped into the garage and called out his friend’s name to let him know he had arrived, quickly shrugging off his jacket and hanging it up on the coat hanger. He then made his way to the bathrooms, where he changed out of his work clothes and into his old coveralls from when he worked at Bobby’s back in Lawrence. They were a bit tighter than they had been four years ago, but it wasn’t terribly uncomfortable or anything. It wasn’t as if he gained that much weight in Chicago; it was just bound to happen as he grew older, right?

His best friend greeted him with a high five before claiming that he was on his coffee break and that the rest of the workers would be able to handle everything without him for the next fifteen minutes. So Dean had happily followed him outside, hesitating before accepting the cigarette that Benny was offering him. He didn’t smoke often, but sometimes he needed it to calm his nerves.

Benny was aware of Dean’s habits, so the moment he lit their cigarettes, he spoke up. “What’s bothering you, brother?”

The blond thought about the question for a while, although he knew exactly what was bothering him. Truth was, Dean wasn’t confused about why he had been clinging onto the idea of ‘Jimmy’. It wasn’t something familiar to him, sure, but it was something exciting; something that gave him hope. Something that made him wonder if he wasn’t going to spend the rest of his life alone after all, and it was a very realistic fear of his now that he was a little over three years away from turning forty years old. “You ever feel like this is all you get? I mean… What you have right now in life is all you’ll ever have to live with? Nothing new, nothing exciting, just… this? He asked after a long pause, puffing out smoke into the cool air.

“Sometimes, yeah. But it ain’t all that bad for me, you know? I got you, my wife, family, and a stable job… I don’t think I need to ask for anything else, ‘cause then I’d probably be asking for too much.”

“Yeah, well--“

“You don’t need a man or a lady in your life to make you happy, Dean. You understand? You’re the one who needs to make yourself happy before anyone else does.” Benny sounded exhausted. He knew he trusted the man too much when it came to talking about these things, but what was he supposed to do? Talk to Sam about it? Because the only thing Sam would do is turn it all into some stupidly romantic speech that made him feel like he was going to barf. Plus, his other two options were talking to Charlie about it and talking to his dog about it, and both of those would options would only be seriously considered if he truly lost it. It took Dean awhile to realize the other man was still talking, and he refocused on his voice, brows furrowing slightly. “So you don’t have any good experiences in the dating department, but soon someone will come along, and that someone will make everything seem so much easier for you, alright? And if they don’t, then you’ve always got me,” he said, offering him a small smile and a nudge with his elbow.

Dean nodded slowly, gulping before he looked away. Benny had a point. He was just overreacting. He had all the time in the world; he didn’t have to find someone right now. He’d have time to get to know whoever he would end up with, and they’d move in together, and start a family, and everything would be fine. Because everything ended up fine for everyone else, so it had to be fine for him.

He could hear Raphael’s voice call Benny back inside, claiming his break was over, so he turned to face the brunette with a small smile. He tossed the cigarette to the ground and crushed it under his heel before clearing his throat so he could speak up. “I owe you one.”

“Don’t sweat it. Now let’s get some work done. Maybe I can even hook you up with some of our clientele; last time I checked, most women and a few men can’t really keep their eyes off of greasy Dean Winchester. “

Dean huffed a laugh at that and rolled his eyes, running his fingers through his messy hair before flattening it and following the brunette inside. It was nice and warm, and the roar of engines engulfed his thoughts. He loved teaching, but that never took away his love for cars. Taking everything apart and piecing it all back together was soothing, and once you got the hang of it, you’re good to go; it was like riding a bike.

He never understood why being a mechanic was as under appreciated as it was, but he didn’t really care, at the end of the day. He was doing this because he enjoyed it, and if anyone had a problem with that, they were welcome to walk out of his life.

...Okay, maybe that was a bit of an exaggeration, but it got the point across; Dean was very proud of his hobbies and his job, and he didn’t need someone who talked him down hanging around him for more than five minutes.

“Winchester! Are you even listening?” Benny asked, his voice loud enough to make Dean jump in his spot. His icy blue eyes glared at him as the blond smiled sheepishly, and he pushed a bunch of forms into his hands. “There’s a guy here, wants to pick up his car. Get him to sign all of this shit, I already talked him through it, and learn how to focus on stuff, will you? You’re bound to get yourself run over in this place if you keep on spacing out for long periods of time,” he sighed, shaking his head. He clapped a hand down on his shoulder, squeezing it quickly before he made his way towards a car that was being brought in at the far end of the repair shop.

He made his way towards the office, papers in his hand, and slipped in behind the desk easily with a small hum. He grabbed a pen before he asked the assistant to buzz in the guy; someone named Castiel James Novak.

“Castiel,” he mumbled, the name feeling odd on his tongue. It rolled off easily, but he wasn’t sure why. It took him a few moments to remember the stories his mother would tell him and Sammy when they were young, about angels watching over them, and a small smile spread across his lips. “Castiel,” he repeated, a little more confidently. 

Mary Winchester loved telling her sons stories about angels and God and demons and ghosts. It was clear that she didn’t believe in them religiously, but she enjoyed the idea of someone being there to take care of her sons when she wasn’t around anymore. Dean was glad she had told them about it all so early in their lives, because he wasn’t quite sure he would have been able to stay strong a majority of the time if he didn’t continuously remind himself that maybe, somehow, his mom and the angels were still watching over him. He let out a small huff at that, twisting the pen in between his fingers and raising his eyes when he heard voices on the other side of the door.

The door swung open, and Dean nearly had a heart attack when the guy walked in. Really? He’d been searching for the guy for over a month, and all he had to do was wait in the damn repair shop if he wanted to see him again?

He let his eyes flicker down to the paper, and he chewed on his lower lip. Okay, so he hadn’t been completely wrong about him when it came to his name; he had called him Jimmy all along, but it just happened to be his middle name instead of his first name. Plus, Castiel may be a mouthful, but it was unique; a name you couldn’t quite forget. Hell, it definitely suited him. The brunette was still very much wearing his work clothes, and honestly, Dean had forgotten how fancy he had looked the first time he saw him. Only this time it was much worse, and the guy was wearing a gray button up with his sleeves rolled up to his elbows, a black tie, the same dress trousers he’d seen him in last time and a frigging waistcoat. Who the hell thought wearing waistcoats during the day was fine? The guy wasn’t even a businessman, he was a professor, and Dean couldn’t think of any professor who always looked like he was dressed to impress.

But boy oh boy, was he impressing Dean. He usually found guys who looked as dapper as him pretentious and boring, but right now? All he could think about was how someone managed to look so damn attractive when he didn’t even appear to be trying. The assistant, Bela Talbot, cleared her throat loudly in a manner that caused Dean to jump slightly in his seat. Okay, right, he had to take care of a client. This was what he was here for.

He stood up, suddenly feeling under dressed in his coveralls even though he had to wear them for work in the garage. “Hey, you’re that guy from my lecture hall,” he started, offering him his usual lopsided grin. He had to admit, he was proud of himself for not stuttering.

“Yes, that is me,” the guy confirmed, shrugging slightly as his lips twitched up just a bit.

He watched Castiel for a few moments before turning his attention to Bela, nodding at her. “Thanks, Miss Talbot; I can take it from here.” She nodded curtly and gave him a once over and a smirk that may have been slightly inappropriate for the work place. Oh, and extremely inappropriate in front of his crush, too. _Crush? What are you, twelve?_ Dean turned his attention back to the blue eyed man in front of him, gulping before he continued talking. “Well, I have to tell you, Castiel, I’m glad I finally figured out what your name is.”

“What? Why?” The brunette tilted his head to the side, squinting his eyes slightly and causing his nose to crinkle.

“Uhm, I just… I never saw you around after that? It was kinda weird, honestly,” Dean mumbled, beginning to look down at the desk. “I’m not creepy, I swear.”

“Don’t worry about it, Dean. I wasn’t going to tell you you’re creepy,” the other reassured him, and Dean’s eyebrows shot up.

“How do you know my name?” He asked, his tone hopeful. Maybe Castiel had been looking around the campus for him, too.

“It says it right there,” Castiel replied, pointing at the name stitched onto his coveralls and making the tips of Dean’s ears turn pink with embarrassment.

“Oh,” he mumbled, rubbing his nape. Yeah, he really was creepy. Plus, what were the chances of this guy being even remotely interested? He settled into the chair and slid the papers across the table before speaking again, “Well, have a seat. I heard Benny talked you through everything.” The older man nodded at that and took the pen Dean offered him.

“Yes, don’t worry. He told me I just have to sign off on a few things and that after that we’ll just have to make sure the engine is running properly before I drive off with my car,” Castiel hummed, his fingers working on flipping through the papers quickly, hand moving swiftly as he signed the dotted lines.

Dean nodded weakly, watching the brunette as the man kept his head down. He could see the laugh wrinkles around his eyes, and he wondered who the hell was able to make him laugh, because he was barely able to get a smile out of the guy. His hands were calloused and rather large, but they were gently holding onto the pen and the corners of the pages, as though one wrong move would cause him to destroy whatever he was holding. His eyes flickered back up to Castiel’s face and he let his tongue flick over his lips before he allowed himself to speak up. “So, Cas, what do you teach?” Cas? Where the hell did that come from?

Castiel seemed to be asking himself the same question, so Dean shrugged apologetically. Though he had to admit, the way the man was cocking his head in confusion was pretty damn adorable. How could a grown man even be adorable? “Your name is kind of a mouthful, in case you hadn’t noticed. I mean, if you’d rather not have me call you Cas, I get it, don’t worry about it.”

“Hm? Oh, it’s fine really. I know saying my full name can be quite annoying, especially if you’ve known me for a while, but… usually it’s ‘Cassie’. No one has ever called me ‘Cas’,” he murmured, brows furrowing in an adorably confused way.

“I can call you Cassie, if you want? Though, honestly, I’d rather not. Makes you sound like a chick.”

“My thoughts exactly,” Castiel replied, and the small twitches of his lips that he had received from him so far turned into a genuine smile. Dean was glad for all the small smiles he had received up until then, because he wasn’t too sure he would have been able to handle it had he managed to make him smile like that every time. “Don’t worry, I like ‘Cas’. I’m not sure how no one was able to think of that name before you, honestly,” he huffed, shaking his head and looking back down at the papers.

“Right…” he mumbled, chewing on his lower lip before trying again. “So, Cas, what do you teach?”

“Oh, yes, my apologies. I teach chemistry.”

“Chemistry, huh? That sounds fancy… and confusing.”

“It’s an interesting topic once you get the hang of it. You seem like an intelligent man, I’m sure you would understand it if it was explained to you properly.”

Dean’s eyes lit up at the man’s comment, but he shrugged at it, trying to play it off as surprise. “I doubt I’m smart enough to understand it.”

“You’re a professor, Dean. I’m fairly sure you have to be clever in order to become a professor.”

“Well, I mean, I’m smart when it comes to certain things… but that doesn’t mean I’d be able to understand whatever the hell it is you’re teaching your students.”

Castiel rolled his eyes at that, but a defiant sigh left his lips. “Fine, I suppose you might not be able to understand it. But you never know; maybe one day you’ll actually be interested in the topic.”

“Yeah, maybe,” he agreed in a murmur, scratching the back of his head.

“What is it that you teach, then?”

“Uh, I teach English language and literature.”

“So you enjoy reading?” Castiel asked, suddenly appearing far more interested than before.

Dean nodded, smiling at the man’s enthusiastic response. “Yeah, I do. It’s a good way to end the day, y’know?”

“Yes, I believe I know exactly what you’re talking about.” The man finished signing the papers and handed them over to Dean before standing up. The blond chuckled at the brunette’s impatience and quickly scanned the forms before standing up and walking around the table to stand a bit closer to him. He didn’t want to be too close, though, because he wasn’t sure he’d be able to handle it.

“Ready to get your car back?”

“Definitely.”

He led the other man towards the car quickly, letting out a whistle at the sight of the vehicle. It was a dark blue 1979 Lincoln Continental, and since they repainted it, it was practically glowing in the dim light of the repair shop. So, Cas had a good taste in cars _and_ he was attractive? Dean wasn’t quite sure that that was fair.

“She’s a beauty,” he hummed, shoving his hands into his pockets.

“Yes, she is. My brother was going to get rid of her; can you believe him?” Castiel asked, clearly scandalized.

Dean let out a low chuckle at that and shook his head. “I really can’t. But he’s lucky he has you around, because it’d definitely be a shame to see a piece like this go to waste,” he hummed. He was looking at the car, but he could see Castiel looking at him excitedly out of the corner of his eye. He was really hoping that he was getting on the man’s good side, because he was definitely planning on visiting the science department more often, and he was hoping the brunette would be glad to see him in those halls.

He handed over the keys, letting out a soft sigh. “Here. Take good care of her this time around, you hear me?” His brows shot up as he heard the man’s low chuckle, filing that sound away for later when the keys were snatched from his fingers.

“You have nothing to worry about, Professor.” The brunette quickly slid into the driver’s seat, shooting Dean another one of his small smiles before starting the car. “Have a nice weekend. Maybe I’ll see you on Monday.”

He didn’t give Dean a chance to reply. He was driving towards the exit quickly, the roar of the engine making him bite his lip as he watched the car turn onto the road. Right. Monday. He was _definitely_ going to see him on Monday.

He was ready to start heading back to work on other cars (and by that he meant he was going to work on Baby) when Benny stopped him in his tracks. His face was bright and there was a suspicious smirk playing at his lips, one that made the blond’s stomach flip uncomfortably. “What?”

“Nothing.”

“What did you do, asshole?”

“Always with the names, brother. I just thought you may appreciate the fact that I’m letting you take care of a hot customer,” he said innocently. But Benny knew. Benny somehow knew that they had met before, and now he was going to be annoying about it.

“Look, he’s hot, alright, but I don’t care. Didn’t we just have a conversation about this?”

“Yeah, you’re right.” Well, that was easier than expected. Usually he’d make fun of him until he finally broke and talked about someone he liked, but the man was giving up far too fast.

“I am?” He asked, the surprise clear on his expression.

“You are. I’m just too tired to mess with you right now,” he hummed, running his fingers through his hair before shooting him another grin. “But don’t you think you won’t have to deal with me some other time, Winchester. I know where you live.”

Dean groaned at that, flipping him off and making his way towards the Impala. It had been a long day, he knew that much; but he couldn’t help the small smile that kept tugging at the corner of his mouth as he popped the hood of his car open.

He was going to take it slow this time. He knew which department Cas was in, and he knew that the guy had at least one thing in common with him. All he had to do was find something else and then they would be able to have plenty of conversations. Okay, he hoped that would be the case. He’d get closer to him, hang out with him more often, and ask him to join Benny and him for a drink… Maybe he would find out that he doesn’t even like Cas. Maybe it was just a way for him to escape the fact that he didn’t have anyone in that way.

But then he thought about the deep voice, the blue eyes, the bedhead, the way he cocked his head and squinted his eyes when he was trying to understand something, the man’s laugh and his smile…

“Nah, Winchester, you definitely like him,” he sighed to himself, but he only ended up smiling even more. Castiel James Novak was going to be the death of him.


	5. Dean Makes Stupid Mistakes

**_ 4th of November 2015 _ **

If there was one thing Dean hated more than grading papers he received from his students, it was getting mixed signals. He had bumped into the brunette on the Monday after he dropped by the repair shop, and ever since then, they had been hanging out in his lecture hall during their breaks. Charlie tagged along with him, of course, but that was only because of Castiel’s friend, Meg. Dean didn’t like Meg. She was cold and calculating, and kept on rejecting the coffee that he brought in for the four of them every morning before the lessons began. Instead she would just talk to Charlie and Castiel lively while Dean sat at the corner of the brunette’s desk.

Castiel wasn’t as obvious as Meg, however. He didn’t show whether or not he enjoyed spending time with him, and it was starting to annoy him. He liked Cas. He _really_ liked Cas, actually, and he wasn’t expecting him to admit to having any feelings for him any time soon. He wasn’t crazy, after all; they hadn’t known each other for too long, and right now they were beginning to see each other as friends. The only thing that really bothered Dean, though, was the fact that he constantly changed from being distant and reclusive to asking him if he wanted to go out to drinks after work or if he wanted to go off campus to get food quickly during the day. Unfortunately, he learned that when he invited him out for drinks, he didn’t mean it as a date. And Meg was obviously picking up on his interest for her friend, because as soon as the hope in Dean’s eyes began subsiding, she would have her hands on Castiel, dragging him along to go get a drink with her while he was left at the booth alone.

Every since that night, he brought either Charlie or Benny with him.

Dean made his way down the hallway of the science department, holding the coffees and pie tightly in his hands. He wasn’t sure why students were already here when it had only just turned seven, but he wasn’t going to ask. No, he was going to spend his time in his friend’s lecture hall until Castiel’s students decided to file in. He had a small smile on his face as he walked, humming to himself as he grabbed the plastic bag with the pie by his pinkie before trying to open the door. If anyone asked him, Dean would say that that had been the first mistake he made. He should have knocked, because if he had, maybe he wouldn’t have seen the way Meg’s lips pressed against Castiel’s cheek. He wouldn’t have noticed the brunette’s blush that much, either. His second mistake, however, was that he kept on walking through the door, apparently causing Castiel to blush even more as Meg scowled at him. Right. So Cas was in a relationship. Of course he was, how would a guy like him not be in a relationship?

“Good morning, Dean,” Castiel hummed as Meg walked past him and towards the door, making him crinkle his nose. Usually he would ask what her deal was, but he was fairly sure he knew now. He doubted most people would be happy that someone was flirting with their significant other on a daily basis, but he was glad that Meg didn’t try to kick his ass. Yet.

“Mornin’, Cas,” he grunted, his voice still low from sleep. He hadn’t had anything to drink that day, and his throat was aching for anything. “How did you sleep?” He asked, setting the coffees down as well as the pie. Cas knows he can’t have any of the pie. They’ve been over it too many times.

“Could have been better, but I’m here, aren’t I?” The brunette hummed with a smile, settling back down behind his desk. He had his small smile tugging at his lips, and an odd surge of jealousy passed through his chest.

“What’s got you so chipper?”

“What? Nothing!”

Dean’s eyebrows shot up as he grabbed one of the chairs and brought it forwards, placing it in front of the desk before he settled into it. “Jeez, if I didn’t know any better, I’d think you were hiding something from me.” Which he was, because he had just gotten proof of that.

“No, I’m not, really. Just… I have had a far easier time here than I thought I would so far,” he said as his smile grew, making Dean cock his head. They had had conversations about their jobs and their siblings (Cas had to deal with four _older_ brothers, apparently, and Dean realized he really was thankful for Sammy), but never about anything else.

“You just moved here this year, right?” The dark haired man replied with a nod. “Where are you originally from, then?”

“Pontiac.”

“Michigan?”

“No, Illinois. It’s why I know Meg so well; we were friends in high school and when she heard I was moving to Chicago, she called me.”

So what the brunette was trying to say was that he never had a chance. Meg was already all over him since before he even had a shot, and all Dean could do now was accept defeat. Not that it would make him like Cas any less, but at least now he would have his boundaries.

“Well, that’s good, you know. If I hadn’t met Benny my first day here, then I wouldn’t have been able to get around this place at all.”

“First time in Chicago?” Castiel asked with a hum, and he nodded in response.

“Yep. Was born and raised in Lawrence, Kansas, and spent most of my summers in Sioux Falls. It’s nothing like Chicago, but I wouldn’t trade it for the world,” he said softly, a weak smile playing at his lips as he thought of his family. “Gonna go see them soon for Thanksgiving.”

The brunette was smiling at him as well, but Dean didn’t notice. He was too busy thinking about how he would get to see Sam again, and his niece, and his sister-in-law and Ellen and Jo and Bobby… “That sounds really nice, Dean.”

He nodded in agreement as he reached for his coffee cup, taking a slow sip from it and cursing almost immediately. He should have waited a bit longer.

“Are you alright?” Castiel’s voice asked almost immediately, and Dean nodded and smiled embarrassedly.

“Yeah, uh, sorry ‘bout that. Anyways, how about you? You goin’ back home for Thanksgiving?”

The untamable brown hair shook from side to side as the man shook his head, and Dean wasn’t able to tear his eyes away until that deep voice of his forced him to. “No, my family would rather not have me back there, actually,” he murmured, plucking at a loose string from his dark blue tie.

He froze for a moment as he looked at the man, brows furrowing. He wasn’t going to ask why, seeing as he was fairly sure they weren’t at that point in their friendship yet, but it made him feel uncomfortable and disappointed. “So where will you be during Thanksgiving?” He asked slowly, not wanting to push the topic. But Cas didn’t seem to mind, and he was fairly sure that the brunette would tell him if he wasn’t comfortable with Dean’s questioning.

“Probably alone. Meg is also going back to Pontiac to see her family, and my brothers are all going to be with my parents.”

Dean Winchester has done quite a few stupid things in his life. Actually, he’s done too many stupid things in life. But right now, he really wasn’t seeing anything wrong with his question. “How about you join my family and I for Thanksgiving?”

Blue eyes began to widen as the brunette sputtered, setting his coffee back down on the desk. “Dean, I couldn’t possibly int--“

“You wouldn’t be intruding, Cas. I’m inviting you because I think you shouldn’t be alone during any holiday.”

“I’ll be fine with staying in Chicago on my own for four days, really.”

“Come on, it’ll be fun. Get to hang out more often, _and_ I’ll get you out of Illinois,” he pointed out, raising his eyebrows and tilting his head slightly as he grinned.

There was a loud sigh from the other side of the desk and Dean clapped a hand on his knee. “Fine. I suppose it won’t be so bad if I leave Illinois for a bit. I’ve been living in this state for forty-two years, I suppose leaving for a few days won’t hurt.”

The blond had finally managed to open his pie box and was mid bite when the older man spoke. Ah. Yes. Older man. By six years. How exactly, Dean wasn’t sure, because the man looked calm and collected and unlike any of the forty year olds he has ever met. He cleared his throat roughly before swallowing the pie and licking his lips, head nodding slowly. “Well, I’d have to call and make sure Ellen is fine with it, but she makes plenty of food; I doubt she’ll have a problem with squeezing an extra plate onto the table,” he assured him with a wink, reaching towards his cup.

Castiel’s warm smile made his heart flutter and the man’s sudden boost of confidence made him feel even better. He never really felt that holidays were important, but Ellen would slap him on the back of the head with a newspaper and say that it was time for families to get together. According to her, it was also a way to keep him off the streets without having to lock him in his room.

“Thank you, Dean. I really do appreciate it.”

“Yeah, man, don’t sweat it. ‘S no big deal, anyways. But, uh…” he fidgeted as he set down the pie on the desk and reached into his pocket, pulling out his phone after a bit. “I should probably have your number, y’know? Just in case,” he mumbled with a sheepish smile. The brunette looked right past his demeanor and held his hand out for the device. Dean placed it in his palm, lips twitching into a wider smile.

“I don’t use my phone too often, to tell you the truth, so don’t expect immediate answers if you text me.” The phone was handed back to him, and soon enough, Dean was texting the brunette so that the other would have his number. The phone buzzed on his desk and he smirked at Castiel’s expression. “Just because it buzzed doesn’t mean I’m going to reply.”

“Just save the damn number, Cas.”

The older man chuckled and shook his head fondly as he reached for his phone, quickly saving his contact under ‘Dean Winchester’ and turning the phone screen to show him. “There. Happy?”

“I’m delighted, yes,” he hummed in response, earning himself a small glare, but soon enough they both burst into a fit of giggles.

They finished off the rest of their coffee in peace, and Dean even offered some of his pie to the older man. He had been shocked, and to be honest, he had surprised himself as well, but luckily he didn’t want any. He didn’t have any classes to teach at eight in the morning that day, so he would have plenty of time to finish everything off before his first lesson of the day.

The students began walking into the classroom, and their conversation about whether or not it was weird that the blond actually kind of liked Taylor Swift was weird or not. Saying that she was talented wasn’t enough of a reason, according to Cas, especially since Dean seemed to be so obsessed with his rock music. _‘She has to have covered some Led Zeppelin song for you to start liking her.’_ He would have responded had he not been interrupted by one of the students.

She was clearly still fairly new, and her excitement was definitely not something she was able to contain easily. Or at all. “Hello, Becky. How may I help you?” Castiel hummed, and Dean immediately memorized his professor voice again. It had been a while since the last time he heard the man use it.

“I was just wondering if… um… Professor Winchester would be joining us today,” Becky chirped, making Dean raise an eyebrow. Her excited smile turned into a wide grin all of a sudden, and if Dean had turned around to look at Castiel, he would understand why.

The man turned to address him, pursing his lips. “You’re free to stay, if you want.”

He had to admit, he did hesitate for a short while before shaking his head. “Sorry, Cas. Got work to do; you know how it is,” he hummed as he slipped his phone back into his pocket and stood up. He shot the both of them a quick smile before grabbing his pie and the empty cups of coffee before Cas could protest.

Becky seemed fairly disappointed, and Dean wondered if she had already managed to develop a crush on him in her short time in the university. He winced at the thought, tossing the cups to the trash as he made his way back to his lecture hall. He had a reputation of being that attractive professor who people saw as immature and willing to take advantage of his female students, and he disliked it immensely. And rightfully so; he wasn’t sure he could think of one sane man his age that would appreciate having teachers and parents constantly watching him because they fear that he had accepted the offer of getting a blowjob just so he could bump up a student’s grade.

For the rest of the day he was able to keep the thoughts of Meg kissing Castiel’s cheek out of his mind. He talked to Charlie, joked around with a few of his students between his lectures, and did his best to stay focused _during_ his lectures, although he wasn’t quite known for being able to stay on topic for too long. Not that his students really cared about that, though, because he was one of the few professors who enjoyed having his students approach him after their classes. He liked speaking to them one on one, getting to know them better outside of the lectures so that he would hopefully be able to understand their train of thought while reading the assignments they turn in.

The school day ends quickly, and he isn’t reminded of anything from earlier that day until Castiel texts him, asking him if he called his family yet. Oh. Right. He invited him to Thanksgiving.

His fingers twitched for a few moments before he finally dialed Ellen’s number, chewing on his lower lip. He hadn’t spoken to Ellen in a while. Sure, he visited Lawrence for a month with Doof that summer, but he had left at the end of July, which was a little over four months ago. He was definitely going to be scolded for this.

“Dean Michael Winchester, where the hell have you been?” Ellen asked loudly as she answered him, making him wrinkle his nose as he shut the door of the Impala behind him.

“I’ve missed you, too, Ellen. I’m fine, thanks for asking,” he murmured, leaning back in his seat.

“Boy, don’t sass me. Start calling more often; you’re never going to be too good for Lawrence, no matter how hard you try.”

“Hey, I don’t think I’m too good for Lawrence!”

“Then start calling more often, maybe we’ll believe you then,” she hummed, making Dean pout with a small huff. “Anyways, how are you? Bobby’s been wondering if you’re even going to bother showing up in a few weeks.”

“’Course I am, why wouldn’t I?” He asked, though from the way Ellen had answered his call, he already knew. “Actually, that was kind of the reason I called.”

“Makes you sound real suspicious, you know. Come on, spill it, what’s going on?”

“Uh, alright, so… I was talking to a friend of mine--“

“Which one?”

“He’s new.”

“What’s his name?”

“Cas.”

“Honey that sounds like a girl’s name.”

“It’s short for Castiel,” he said in an annoyed tone, and he could hear the surprise in Ellen’s voice is she spoke up again.

“You’re slightly protective, aren’t you? Anyways, you sure he’s just a friend?”

“Yes, Ellen, I’m sure.”

There was silence on the other end, and Dean cleared his throat as he started speaking once again. “Anyways, we were talking about break, and, uhm, turns out he can’t go back home ‘cause his folks don’t want him there, so--“

“You’re dragging his ass over here, is that clear?” She asked quickly, and Dean’s lips tugged into a wide grin. Ellen Harvelle was one of the best women he had ever met, and boy, was he lucky to have been raised by her.

“You’re the best.”

“Don’t waste my time by telling me things I already know, boy,” she laughed, and Dean could imagine the fond smile on her lips. He really did miss home.

“I should probably start driving back to my place… You know, before my dog decides he can’t keep it in any longer.”

“Sam told me about him. Sent a picture, too. You’re dragging his fluffy ass here, too, right?”

Dean let out a low chuckle, nodding even though she couldn’t see him. “Yeah, I am, don’t worry.”

There was a pleased hum on the other side of the line, and then a throat was cleared. “Alright, I won’t keep you from going back home. But remember to call me more often, or even send me a text or something. I’m sure I can get Jo to help me out with it.”

“I will, don’t worry. Say hi to her and Bobby for me, will you?” 

“Sure thing, Dean. I’ll see you real soon.”

“See you, Ellen.”

He hung up quickly so that he could scroll into his messages, fingers tapping excitedly as he looked at the screen. He wasn’t even dating the guy, and yet he was way too excited about the fact that he was going to meet his family. He was going to meet Ellen, and Bobby, and Jo, and Sam, and Jess, and little Mary… He really did need to call them all more often.

He opened a new message, licking his lips and hesitating before typing out a message.

**_From: You_ **

**_To: Castiel Novak_ **

_< \- Hey, so I just talked to my ‘aunt’ Ellen, and she says you’ve gotta come, so, you know… that kinda means you have no choice._

_< \- But seriously, you have to join us. Spending any holiday alone ain’t fun at all._

He was about to pull out of the parking lot when his phone chimed with a text message, a response from Cas. “That was fast,” he mumbled in surprise, but he was still grinning like an idiot at it. 

**_From: Castiel Novak_ **

**_To: You_ **

_- > Thank you, Dean. Tell your family that I appreciate it._

_- > I suppose we’ll discuss the details later on?_

**_From: You_ **

**_To: Castiel Novak_ **

_< \- Yeah, definitely. I’ll see you later, Cas._

* * *

Dean walked into Castiel’s classroom the following day, as usual, with two cups of coffee and his box of pie. Meg pushed past him once he opened the door, and he was lucky not to have spilled any of the coffee on himself, because that would have resulted in a really bad burn. The brunette seemed to notice his confused look, and he shrugged an apology.

“She doesn’t have anything against you, you know. She’s just… awfully protective,” he explained, making Dean huff.

“You’re a grown man; she knows you can take care of yourself, right?”

Cas smiled and nodded at him, running his fingers through his hair as they settled into their usual seats.

They chatted about their lessons from the previous day, taking turn in making fun of their students. “Man, you should have seen Kevin’s face. The kid’s a genius, and Bela just kept on spitting out random definitions for simile, and he looked like his head was about to explode,” he laughed, making the older man chuckle as well. Holy shit, he doubted he’d ever be able to get over that laugh. It was low, and his chest rumbled with every sound that he made, and good god he couldn’t help but wonder what that would feel like if his lips had been wrapped around him instead.

“Dean? Is everything alright?” Castiel asked, a worried expression on his face as he looked over at him. Of course he was worried about him; he was daydreaming mid-conversation, and worst of all, it was about the guy in front of him. “You look a little pale.”

“Dude, you’ve got nothin’ to worry about. I’m just a little tired. I end my day early today, so I’ll be gone as soon as my last lecture is over,” he assured him, taking a cautious sip of the hot coffee. The brunette didn’t seem convinced, but thankfully, he didn’t comment. Instead, he returned to their previous topic of conversation. He was already packing up, anyways, so if the other didn’t want to answer him, it’d be fine; he’d be on his way out of the class, anyways. Chewing on his lower lip, he hesitated before asking the question. “So, did you find out why Becky wanted me to stick around yesterday?” He was already on his feet, coffee in one hand and the bag of pie in his other.

The other man blushed - actually _blushed_ \- and cleared his throat. “She wanted to know why you didn’t want to stick around if you liked me so much,” he said quietly, eyeing his coffee cup.

Oh. _Oh_. He had completely forgotten that she was in one of his classes, so she had been there the entire time when he was practically whining about not being able to find Cas around campus again. _Wait, if she’s in his class then that means she knew where he was this entire time_. “Sonuvabitch,” he mumbled, making Cas raise his eyebrows. 

“What?”

“Uh, nothing, she’s just been using that line with a lot of the other professors around here, too. For her third month in this school, she’s already managed to get me caught up in a few dramas,” he chuckled, making Castiel nod curtly. “Hey, I should get goin’, see you later.”

He didn’t give the other man time to respond. He just kept walking, out the door, down the halls, and back towards his lecture hall, where he would be far away from the next question that was probably going to follow his answer. _Was she telling the truth?_

So instead he settled back in his chair, lazily speaking to his class, letting them work on their latest essays before he rested his head on his table and let himself relax.

Dammit, he was completely screwed, and Becky knew it. Ellen probably knew it, too, and he doubted that Meg didn’t know how much he already liked Cas. The only person who didn’t know was the man himself, actually, and now that he was thinking about it…

Thanksgiving was a terrible idea.

“Too late to turn back now,” he mumbled, sitting up and dismissing his class so that he could go home for the day.


	6. Happy Thanksgiving (Part 1)

**Notes for the Chapter:**

> Hey guys, sorry it took me so long to upload this! I've just been extremely busy with work and all, but I hope this kind of makes up for it. I'm hoping to get the second part of this chapter up at some point during this next month, and I'm going to try to get a regular posting schedule going.
> 
> Here it is for now, though, so enjoy!

**_ 26th of November 2015 _ **

 

The weeks leading up to Thanksgiving were… awkward, to say the least. Dean would go to the repair shop every Friday, then go out for drinks with Charlie, Benny, Castiel and Meg, and then finish off his day in bed with some girl or guy he didn’t know because he was too drunk to remember talking to them. He would spend his Saturday mornings at home with a few bottles of water, a cup of coffee, and a very annoyed dog on his lap while he texted his friend to apologize for disappearing the previous night.

 

He was so sure that he had stopped sleeping around, that he was past all of that, but the moment he saw Cas with Meg, all the things he told himself about him being ready to settle down seemed… wrong. He would leave early so he wouldn’t have to see them look so happy around one another, though he would assure everyone that it was just because whoever he had managed to find wanted to get out of the bar as soon as possible. And who was he to deny them pleasure, right?

 

Benny noticed the change in him. He definitely was not too happy, either. He would send annoyed glares at him whenever Cas and Meg looked away, or whenever they began speaking about the blue-eyed man.

 

God, his blue eyes were beautiful, weren’t they? Not that he was saying other things about him weren’t attractive. His features were beautiful, honestly; from the sharp jaw, to his perfectly modeled Greek nose, and his flawlessly tousled hair, Castiel James Novak was pretty much the hottest guy Dean has ever met. And then, of course, he had to add in the frigging bluest-blue-to-ever-blue eyes that caused him to stare a bit too much. Though, if he was being completely honest, he was starting to think there would never be a time where he would allow himself to admit that he was staring at the man too much, because really, there was no way that there could ever be too much of it. Castiel had a face that still blew him away, no matter how many times he looked at him. Not to mention the fact that now he had him on Facebook, too, and… well, not that he was a creep, but the guy had photos of him on his account, so didn’t that mean he wanted people to take a peek? Because he was _definitely_ taking a peek.

 

Anyways, where was he? Ah, right, yes: Thanksgiving, 2015.

 

Dean had parked his car right outside Castiel’s apartment building before stepping out to wait for him at around eight in the morning. He rolled down the window just a bit, letting Doof’s head stick out of the car, before he leaned against the door on the passenger’s side of the Impala, hands tucked in his pockets as he tried his best not to look like he was freezing. He needed to look calm, and cool, and dammit he was acting like a teenager all over again. He felt like he was taking Lisa back to his house so that she could meet his family for the first time, except he and Cas were friends. Ellen and Bobby would interrogate him like they interrogated Lisa, and Jo would walk around staring. Except he and Cas were just friends, and Jo would probably be very interested in getting her mouth on his mouth. Maybe a bit too interested for Dean’s liking, now that he was thinking about it.

 

 

He wondered what Cas thought about his family inviting him over for the holiday. He knew that it wasn’t something completely out of the norm for Ellen to do, but of course, she at least got to know whoever she had invited into her home before deciding that she was willing to feed yet another stomach.

 

Well, as long as no one touched his pie, Dean really could not care less.

 

Not that it was much of a surprise, since he tended to daydream quite often, but he was definitely caught off guard when he saw Castiel. The older man was usually dressed in his work clothes, even after workdays when they went out for a few drinks, but right now? Right now he was wearing a dark blue Henley with a suit jacket above it, a pair of black jeans, and a winning smile. He never thought casual clothes would work for Cas, but boy was he wrong. He wasn’t sure what he preferred seeing him in, but all he knew was that Cas would most likely be able to pull off any frigging outfit he tried on.

 

“Hello, Dean,” he hummed as he walked up to him with a duffel bag hanging off his shoulder, hands held out at his sides as he spun around on his heel quickly. “What do you think?”

 

“Uh, hey, man,” he replied awkwardly, rubbing his nape as he watched the older man. What a… a frigging idiot with a dumbass angel name. Who does he think he is? Making his heart leap like it was no big deal, like he made people want to melt into a puddle of adoring tears all the time. “I think you look great. Less stuck up,” he joked weakly, voice cracking as he spoke. He cleared his throat roughly and shoved his hand through his hair, shifting off of the door of his baby in order to open it for him.

 

“I appreciate your honesty,” Cas chuckled, raising his eyebrow in surprise as Dean made his way to take the duffel bag from him. “It is quite alright, I assure you. I think it’s best if I do some things on my own this trip, seeing as you are letting me join your family for Thanksgiving _and_ you’re driving me there.”

 

“Well, how on earth would you have gotten there otherwise?”

 

“I’m sure I would find a way if you gave me your address, you know. It shouldn’t be too difficult to get to Lawrence.”

 

“Aw, come on, driving all the way to Lawrence all on your own ain’t fun at all,” he sighed as he snatched the bag from the older man, ignoring the huff of annoyance as he opened the trunk and tossed it in.

 

“I presume that is true, but I am fairly certain that I would be able to find my way to Lawrence from the airport had you agreed to me getting flight tickets for the both of us.”

 

Dean shuddered as he watched Cas slide into his seat and shook his head, opening the door to the driver’s seat and quickly sliding in. He really hated planes. “Don’t even make me think about that option. Humans weren’t made to fly, and you know it’s true,” he grumbled as he slammed the door shut, startling himself and his dog. He pet the car’s dashboard before turning and stroking Doof’s head gently, a small, guilty smile tugging at his lips. “Cas, meet Doof. Doof, this is the guy I was telling you about,” he joked, looking over at Cas who was staring at his dog with wide blue eyes.

 

The man leaned over the back of the seat, his expression far too serious, and reached a hand out to take the dog’s paw. He shook it firmly before saying, “it’s a pleasure to meet you,” and Dean laughed harder than he had in a very long time. Being attracted to people really could do a number on your judgement of what was sweet and what was borderline insane. Though, in all honesty, he was happy to see the man trying; if he was being this nice to his dog, what would he be like around his family?

  
He started up the car again, watching as Cas lifted Doof over the back of the seat and brought him to the front. He watched them interact curiously, enjoying the way his eyes would glow when the dog nudged him or bounced back and forth from his lap to the middle seat of the bench. He tore his eyes away after a minute or so and pulled out of the parking lot, turning on the radio so that they would have noise that could fill the silence. Not that it was an uncomfortable silence in any way shape or form; it was just that he always enjoyed having some sort of buzz he could focus on in the background. It was an eight-hour drive anyways, so they would definitely have plenty of time to talk during their trip.

 

It was clear that Cas was just as tired as he was, and when he looked over at the man while they were waiting at the traffic light, he gave him a small nod. “Don’t worry about me, just go to sleep; I’ll wake you up when we get to the Mississippi river, we can stop at some diner in Missouri,” he told him. The tension in the older man’s shoulders faded away and when the bright blue eyes were finally hidden from view, Dean let himself take in the image. He was peaceful, and there was a small frown permanently etched into his lips as his face slowly relaxed. He had forgotten to shave that day, and it was obvious from the stubble on his cheeks, the dark hair offering a sort of contrast to the man’s skin. Not that it was pale in any way, of course, but his hair still managed to seem startlingly dark against it.

 

The light turned green sooner than it should have and Dean was forced to pull his gaze away from the angel sleeping in his car, turning up the music slightly and tapping his fingers on the wheel. He had driven back and forth between the two cities so many times that his body was doing all the work almost automatically, which meant his mind was allowed to drift. He smiled to himself as he thought about what having Cas by his side every road trip would be like. He could probably get used to it very easily, and he is slightly surprised that he hasn’t made it a tradition yet. Though, to be fair, he doesn’t want to come off as clingy. Or maybe he already has? He did not know for sure, but what he did know was that he was overthinking things now and that definitely cannot get him anywhere.

 

So he stopped thinking and instead decided to sing along to Pink Floyd, a small smile gracing his lips as he quickly pet Doof’s back and leaned back into his seat.

* * *

 

Two things came to Dean’s mind when they finally reached Hannibal, Missouri: one was that he was far too hungry to function at that very moment, and two was how the hell had Cas not woken up yet? They had been driving for almost exactly five hours and he had only woken up once around two hours ago to pet the damn dog. He was slightly heartbroken when he realized he would have to disturb the older man, but then again he really could not care less since he was thinking with his stomach rather than with his brain. He shook his shoulder, watching blue eyes flash as he looked around the car. “We’re here, get your ass out of the car and into that diner.”

 

“Good morning to you, too,” Cas grumbled, stretching his arms before opening the door of the car and shutting it as fast as he possibly could so that Doof wouldn’t be able to jump out after him. Dean got the leash and hooked it to the dog’s collar easily before getting out with him, watching as he shook his whole body with an amused smile.

 

The two men chose to sit close to a window in the diner, mostly because they didn’t want to be too close to the kitchen because God knows what Doof would have done if he managed to get free and run through the damn door. There wasn’t much talking going on until they got their orders down, and even then, Dean could barely focus on anything other than the rumbling of his stomach.

 

“You could have woken me up earlier, you know. We could have gotten something to it an hour or two ago,” the man in front of him hummed, and all Dean could do was glare.

 

“I didn’t want to wake you up, alright? You looked tired, I thought I’d be able to wait a bit longer.” Clearly he was wrong.

 

The food arrived only ten minutes after they ordered it (although it felt like a lifetime to him), and he wasted no time in grabbing a handful of French fries and unceremoniously shoving them into his mouth. Cas had an amused smirk on his face, and Dean could not be bothered with whether or not he looked like a complete idiot. Yes, he was usually hungry, but he had skipped dinner the previous night out of excitement and he didn’t wake up early enough for breakfast that day. He was allowed to be as disgusting as he wished.

 

Once they both managed to get some of the food down, he cleared his throat, turning to fully face blue eyes. “So…” He started, brainstorming conversation topics. He had a few questions on his mind, two in particular, but he wasn’t entirely sure he should be asking them. He would be prying into his personal life if he dared ask, and he was fairly sure that Castiel would not appreciate it. But, then again, he _was_ spending Thanksgiving with Dean’s family, so… “Why aren’t you celebrating Thanksgiving with Meg or something?” He asked, trying to be as nonchalant as possible. It would have made sense for him to spend Thanksgiving with his girlfriend’s family, but Cas didn’t even seem to make it an option when they talked about Thanksgiving arrangements at the beginning of the month.

 

He watched as dark brows furrowed, his jaw moving as he tossed another fry into his mouth. “Well, her family doesn’t exactly like me,” the man said with a small shrug, and Dean couldn’t help but huff as he brought the burger up to his lips. He took a bite, holding back a loud groan of appreciation before washing down the food with the milkshake he had gotten.

 

“What, so your girlfriend’s family doesn’t like you? Been there,” he said with a small chuckle, though calling her his girlfriend out loud did sting a bit more than it should have. The man’s brows furrowed even more, however, and Dean was immediately intrigued. “What?”

 

“You called her my girlfriend.”

 

“Yes.”

 

“We are talking about Meg, yes?”

 

“Yup. Am I getting something wrong here?” Oh, God, he really hoped he was getting something wrong.

 

“Entirely. First of all, Meg is nothing but a friend. Never has been and never will be; it has been that way for the past twenty-six years and will stay that way.” Dean was definitely popping the champagne in his mind at that very moment. Then again, he shouldn’t be getting too excited. The guy could still have a secret wife or something. “And secondly, she isn’t my type.”

 

“What do you mean?”

 

“I mean I’m not attracted to her. Or any other girl, really.”

 

Dean’s eyes widened and his jaw slackened slightly. Was he saying what he was hoping he was saying? “Are you…”

 

“Gay?” Cas completed for him, his eyes narrowing and lips pursing. “Yes. Problem?”

 

God no. No problem at all. This couldn’t be less of a problem, actually. “Of course not, I just… I really thought you guys were dating, that’s all,” he said once he cleared his throat, taking another bite of the burger in order to busy himself.

 

Castiel simply nodded at him and took a bite out of his own food, studying his face carefully. He wondered if he was turning a bright red or if he had some sauce on the corner of his mouth, and he was beginning to wish that he could slowly blend into the booth bench behind him and disappear from the man’s sight.

 

He was beyond happy at the revelation, really, he was, but now he was aware that he would constantly wonder whether or not the other liked him in the same way Dean liked him. Was he just a friend? Did Cas find him attractive? Or had he managed to make a fool out of himself in a way that made Cas decide there was no future between them, even if he did find Dean attractive?

 

There he was, yet again, overthinking simple things. He shook his head and squeezed his eyes shut, smiling at the older man once he was able to regain his focus. This was them developing a friendship. All this was was a stupid crush he had managed to develop on him and nothing more would ever happen between them.

 

“Is that why your parents don’t want you at Thanksgiving?”

 

Cas nodded, his jaw moving slowly as he chewed his food. “They aren’t interested in having me back in their home until I have decided to lead life the ‘right way’.”

 

“Damn, wouldn’t have seen that one coming from a couple who named all their kids after angels,” he murmured sarcastically, earning himself a laugh from the other. His smile grew a bit more confident after that, and he leaned back in his seat comfortably, chatting with the older man in a way that he had hoped would help him ignore the confession he had gotten only a minute earlier.

* * *

 

They finished their food roughly thirty minutes later and were back on the road in no time, the hum of the car soothing as they got closer to Lawrence, Kansas. They talked about students, schools and even strange encounters they had had with students as they made their way through Missouri, and once they arrived at Kansas City they began discussing Dean’s home and relatives. “You have nothing to worry about, I promise. I mean, they’re kinda scary at first but you grow to love them whether you want to or not,” he joked, glancing over at Cas.

 

“If they are anything like you then I am sure I will be able to get along with them in no time.” That made Dean blush lightly, and luckily the other didn’t seem to notice since he was too busy staring outside the car window.

 

“You sure know how to charm the pants off of people so it’s not like they’re gonna hate you,” he teased, running his fingers through his hair.

 

That made Cas sit up a bit more, and Dean could already picture the confused expression on his face. They were in Grant, Kansas, meaning they had roughly eight minutes until they reached his home. “I wasn’t trying to be charming, Dean.” He finally said after two minutes of anticipation.

 

He frowned slightly, looking over at the older man and knitting his brows. “I know, but I mean, that ain’t exactly something people just say casually, you know? You manage to be charming even if you don’t actually wanna be.”

 

“Well I wasn’t attempting to be charming.”

 

“Alright.”

 

“I was being serious.”

 

“Got it.”

 

He took another pause, staring into the open road ahead of them. Two more minutes. Dean could already feel his chest ready to burst from excitement, and he reached over to pet Doof’s head. Right as he was preparing to announce their arrival to Cas, a warm hand settled on top of his own and closed around his fingers, causing his eyes to widen as he turned towards the other. “You are a kind man, Dean Winchester, and I will always be extremely grateful for your hospitality. I hope you know I am being entirely sincere.”

 

Dean licked his lips and nodded gently, trying to find his voice. That was far more dramatic than it should have been, and now that he was thinking about it, they were closer than they had been before. Much, much closer. If he shifted to his right and Cas shifted to his left, Dean could easily close the distance between the two of them. But just as he was about to ask if he could, Cas shifted away from him and smiled gently, nodding his head towards the house. “They are expecting us,” he said, removing his hand as Dean turned to face the people rushing out of the small house.

 

Turns out his little crush wasn’t so little after all.


End file.
